Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts
Published version
Peer-reviewed
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Repository DOI
Type
Article
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Authors
Davis, HJ
Mihai, MT
Phipps, RJ
Abstract
The use of noncovalent interactions to direct transition-metal catalysis is a potentially powerful yet relatively underexplored strategy, with most investigations thus far focusing on using hydrogen bonds as the controlling element. We have developed an ion pair-directed approach to controlling regioselectivity in the iridium-catalyzed borylation of two classes of aromatic quaternary ammonium salts, leading to versatile meta-borylated products. By examining a range of substituted substrates, this provides complex, functionalized aromatic scaffolds amenable to rapid diversification and more broadly demonstrates the viability of ion-pairing for control of regiochemistry in transition-metal catalysis.
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Keywords
0302 Inorganic Chemistry
Journal Title
Journal of the American Chemical Society
Conference Name
Journal ISSN
0002-7863
1520-5126
1520-5126
Volume Title
138
Publisher
American Chemical Society
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Sponsorship
Engineering and Physical Sciences Research Council (EP/N005422/1)
Engineering and Physical Sciences Research Council and Pfizer (CASE studentship), AstraZeneca (AZ-Cambridge Ph.D. Program studentship), Royal Society (University Research Fellowship), Engineering and Physical Sciences Research Council and Engineering and Physical Sciences Research Council U.K. National Mass Spectrometry Facility (Swansea University)